반응 #2469287

반응 방정식

3-methyl-1H-pyrrolo[3,2-c]pyridine

KOtBu

DMF

BOC2O

→

3-methyl-pyrrolo [3,2-c]pyridin-1-yl amine

수율 35.0%

반응 조건

후처리

1. 1
   기타is purged with N2
2. 2
   workup.ADDITIONChloramine in ether (0.15 M, 145 mL) is added
3. 3
   workup.STIRRINGthe mixture is stirred for 20 min
4. 4
   온도The reaction is cooled to 00 C
5. 5
   workup.ADDITIONand a solution of Na2S2O3 (800 mg) in water (130 mL) is added
6. 6
   workup.STIRRINGThe mixture is stirred for 10 min at 00 C
7. 7
   농축, and then concentrated in vacuo
8. 8
   기타The residue is triturated in DCM
9. 9
   여과filtered
10. 10
    workup.ADDITIONDCM is added to the filtrate
11. 11
    온도cooled to 0° C.
12. 12
    농축The mixture is concentrated in vacuo
13. 13
    기타the residue is purified by silica gel chromatography
14. 14
    세척eluting with 10% MeOH in DCM

실험 절차

A mixture of 3-methyl-1H-pyrrolo[3,2-c]pyridine (1.91 g, 14.47 mmol) and KOtBu (3.25 g, 28.9 mmol) in DMF (65 mL) is purged with N2 and stirred at rt for 2 h. Chloramine in ether (0.15 M, 145 mL) is added and the mixture is stirred for 20 min. The reaction is cooled to 00 C. and a solution of Na2S2O3 (800 mg) in water (130 mL) is added. The mixture is stirred for 10 min at 00 C., and then concentrated in vacuo. The residue is triturated in DCM and filtered. DCM is added to the filtrate, cooled to 0° C. and treated with BOC2O (793 mg, 3.6 mmol). The mixture is concentrated in vacuo, and the residue is purified by silica gel chromatography eluting with 10% MeOH in DCM to afford 3-methyl-pyrrolo [3,2-c]pyridin-1-yl amine (842 mg, 35%). MS: 148 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.85 (s, 1H), 8.36 (d, 1H), 7.32 (d, 1H), 6.95 (s, 1H) 4.77 (s, 2H), 2.37 (s, 3H).

출처